Top 10 Saddest One Tree Hill Moments

“Danny Boy”

Who could have expected to feel anything but joy at the demise of the show's ultimate villain, Dan Scott. He reveled in destroying the lives of everyone around him, and needed to be in control of everyone and everything. When Dan almost died in a fire, every single person in his life became a suspect that he relentlessly patrolled. But after his years of searching for redemption and one final act of heroism in saving Nathan from his captors, you can't help but feel a little sad when Dan finally bites it. Even Haley feels some compassion for him. And Keith returns to usher him into the afterlife as his plus one.

“The Last Day of Our Acquaintance”

It is such a blow to the James/Scott family when Haley's mom passes away. She is the one that stood up for Nathan and Haley when they wanted to get married in high school. In the handful of times we get to see her on the show, she makes a big enough impact that you can’t help but mourn with the family as they hold vigil at her bedside. As a bit of a consolation, Lydia’s passing did manage to bring the James sisters closer together, but it launched Haley into a downward spiral of depression that was difficult to watch.

“The Wind That Blew My Heart Away”

Since the very beginning of the show, we see the pain Peyton has dealt with growing up without a mother, so when Ellie comes along, it is a beautiful thing that she has a second shot at a mother daughter relationship. They have crazy adventures together, and create an entire album together, but Ellie never gets to hear it. When Peyton goes to see Ellie to deliver the finished album, she finds Ellie lifeless in her home. The way the sound lowers and the focus shifts to Peyton crying in the background is cinematically designed to be as heartbreaking as possible. Having her adoptive mother taken away while Peyton waited to be picked up from school was bad enough, but to then lose her biological mother so prematurely, that was just too much.

“Almost Everything I Wish I'd Said the Last Time I Saw You”

Clay and Quinn were a couple that came in late to the game, but they quickly became just as epic a couple as any of the others. But, in the show’s nature, when things seem to be at a high point for them, they are quickly knocked down. Clay’s stalker Katie, who looks uncannily like his late wife, surprises the both of them, and seemingly takes their lives just in time for the season seven finale. Thankfully, both of them survive, but the ongoing uncertainty and potential of losing this power couple really did have us worried for a couple episodes there.

"The Show Must Go On"

Nathan and Haley's second wedding was a roller coaster of emotion. It’s a wonder anyone enjoyed the festivities with all the drama. After a harsh breakup with Cooper, Rachel decides, in classic fashion, to make herself the center of attention, causing a scene, stealing the wedding limo and lying about being pregnant. Nathan and Haley dodge the drama and blissfully take the high road towards their honeymoon. But the wedding bliss ends abruptly when they nearly collide with the limo which then soares over the bridge and into the river. As the limo sinks with Rachel and Cooper still inside, Nathan jumps in to save them. The season ends on a cliffhanger with several lives hanging in the balance. We were almost as devastated as Haley.

"Some You Give Away"

The state championship should have been the best night of all the Tree Hill gang's lives, but it ended in tragedy. When Nathan wins the game, Daunte, the loan shark he owes money, tries to take out his revenge by running Nathan down with his car. But at the last second, a pregnant Haley pushes him out of the way and takes the hit. Completely devastated at the sight of his best friend lying in the street, Luke’s heart gives out and he collapses too. Meanwhile, Nathan takes his anger out on Daunte, before Dan steps in. The whole gang spends the night in the hospital with, yet again, several lives on the line.

“The Tide That Left And Never Came Back”

If Luke and Peyton weren’t destined to be together, Peyton and Jake could have easily been endgame. So watching him have to leave her again and again was absolutely heartbreaking, especially knowing what she’s been through. This time was particularly devastating because we got to watch them really fall in love, only to be torn apart when Nikki returns to steal Jenny away. Who didn't sob like a baby when Jake and Peyton had to say goodbye in her bedroom? Especially after Jake’s speech about how full of greatness she is. Things were finally looking up for them, but Peyton is left heartbroken again.

"Get Cape. Wear Cape. Fly"

Q wasn’t even one of the show’s leads, yet his passing devastated every other character on the show and left a hole in all of our hearts. He started out almost as a villain, but quickly became a beloved hero, cape and all, who was taken away in an act of senseless violence. His relationships with Nathan, Haley, Luke, and Skills made this loss a hard one, but it was his friendship with Jamie that really hit us all right in the feels. Admit it, when Jamie put the cape he made for Quentin on his coffin we all cried even harder than Brooke.

"Darkness on the Edge of Town"

Brooke is a fan favorite character that has had arguably the most well developed character growth in the show, so the thought of losing her is unthinkable. When a car accident during a storm sends Jamie and Brooke into the river, Brooke forces Julian to save Jamie first, risking her own life. For a few terrifying minutes, it seems Brooke might not wake up and Julian’s fierce desperation makes it too tragic to watch. Hearing Jamie come to the scary conclusion himself will make your heart drop right out of your chest.


Before we unveil our top pick, here are a few honorable mentions:

Haley Leaves Nathan to Go On Tour

Jimmy’s Funeral

Lucas and Brooke Break Up

Haley Tells Nathan She Wants a Divorce

Peyton’s Video to Her Daughter

"With Tired Eyes, Tired Minds, Tired Souls, We Slept"

This entire episode is an absolute tear jerker. From Peyton hiding out in the library, to Brooke feeling helpless in the gym, to Jimmy's speech in the tutor center. All of it is enough to have you reaching for the 3-ply tissues. But the climactic moment in the hallway between Jimmy, Keith, and Dan deserves the top spot on this list. Jimmy’s monologue is so powerful, you can’t help but feel compassion for him despite his actions, and crushing sadness as he reaches his wits’ end. But the heartbreak doesn’t end there. Dan then, ending Keith’s life out of pure vengeance was a dark and distressing twist that none of us expected, and that changed everything.